Photochemical Preparation of Novel Tetracyclic Indenoquinolines from Benzotropolone Derivatives

Photochemical Preparation of Novel Tetracyclic Indenoquinolines from Benzotropolone Derivatives

Franco, Jaime; Tabarez, Carlos; Chakrabarty, Shubhashis; Croft, Michael S.; Moyna, Patrick; Moyna, Guillermo

Abstract:

Heteroatom-bearing tetracyclic backbones are important scaffolds for a number of biological targets. These compounds have been widely used as antimicrobial and anticancer agents, and include tetracycline antibiotics and topoisomerase inhibitors. We have shown that a novel class of tetracyclic tetraindenoquinolines could be obtained through photoisomerization of benzotropolone derivatives. In this presentation we detail the preparation of a series of these compounds as well as the corresponding indenoquinolines (Figure 1), and discuss their biological evaluation.

Heteroatom-bearing tetracyclic backbones are important scaffolds for a number of biological targets. These compounds have been widely used as antimicrobial and anticancer agents, and include tetracycline antibiotics and topoisomerase inhibitors. We have shown that a novel class of tetracyclic tetraindenoquinolines could be obtained through photoisomerization of benzotropolone derivatives. In this presentation we detail the preparation of a series of these compounds as well as the corresponding indenoquinolines (Figure 1), and discuss their biological evaluation.

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DOI: 10.5151/chempro-14bmos-R0075-1

Referências bibliográficas

• [1] 1) Hochstein, F. A.; Stephens, C. R.; Conover, L. H. ; Regna, P. P.; Pasternack, R.; Gordon, P. N. ; Pilgrim, F. J.; Brunings, K. J.; Woodward, R. B. J. Am. Chem. Soc. 1953, 75, 5455-5475.
• [2] 2) Lown, J. W. Pharmacol. Ther. 1993, 60, 185-214.
• [3] 3) Tabarez, C.; Waterman, C.; Rapp, A. L.; Moyna, P.; Moyna, G. Tetrahedron Lett. 2009, 50, 7128-7131.
• [4] 4) Khrizman, A.; Slack, R. D.; Remsing, R. C.; Little, S.; Yardley, V.; Moyna, G. Arch. Pharm. 2007, 340, 569-576.

Como citar:

Franco, Jaime; Tabarez, Carlos; Chakrabarty, Shubhashis; Croft, Michael S.; Moyna, Patrick; Moyna, Guillermo; "Photochemical Preparation of Novel Tetracyclic Indenoquinolines from Benzotropolone Derivatives", p-75-75. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0075-1